$1,249,500

23761 Winding Way Milton, DE 19968

Estimated payment $7,031/month

Total Views 5,516
4 Beds
5 Baths
8,057 Sq Ft
$155 Price per Sq Ft

Highlights

  • Guest House
  • Indoor Pool
  • 7.47 Acre Lot
  • Milton Elementary School Rated A
  • View of Trees or Woods
  • Contemporary Architecture

About This Home

TRANQUIL FOREST RETREAT! Discover the perfect blend of privacy & location from this lovingly maintained 7.47-acre property near Redden Forest. This serene retreat offers a park-like atmosphere that’s cool in summer and cozy in winter. Featuring a magnificent 8,057 square foot custom-built main house and a charming 532 square foot guest cottage will an additional full bath, kitchenette & sunroom, there is plenty of space for guests, friends, or extended family. Just a 30-minute drive from The Rehoboth Beach boardwalk and Cape Henlopen State Park, it provides an ideal balance of privacy and convenience, allowing you to enjoy nature's tranquility while being close to vibrant coastal attractions.
The main house offer 4 levels of spacious living, complete with an oversized three-vehicle garage, including a bay with a 20-foot door that can house your RV or boat. Inside, an elevator ensures accessibility across most levels. Luxurious amenities abound, such as an indoor spa with a vaulted ceiling, maintained by a premium Desert Aire system, and an adjoining greenhouse. The great room features a two-story ceiling and expansive forest views, while large windows fill the home with dappled sunlight. The open-concept kitchen is perfect for entertaining, featuring soft-close cabinetry and ample storage. A spiral staircase leads to a third-floor study offering a peaceful retreat with views of the tree canopy.
Enjoy cozy gatherings under the stars from the outdoor fire pit with circular stone seating. A short stone path leads to a separate guest cottage, ideal for visitors or creative projects. This one-of-a-kind designed estate blends natural beauty with practical comfort. The possibilities abound for you to add your own personal touch on making this incredible property your personal retreat! Call and schedule a showing today!

Listing Agent

Lee Ann Wilkinson

(302) 278-6726 leeann@leeanngroup.com Berkshire Hathaway HomeServices PenFed Realty License #RA-0002064 Listed on: 08/08/2025

Berkshire Hathaway HomeServices PenFed Realty

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $4,567

Year Built

  • Built in 2006

Lot Details

  • 7.47 Acre Lot
  • Lot Dimensions are 225.00 x 1074.90 x 399.23 x 1035.44
  • Extensive Hardscape
  • Private Lot
  • Sprinkler System
  • Wooded Lot
  • Property is zoned AR-1

Parking

  • 6 Garage Spaces | 4 Direct Access and 2 Detached
  • 10 Driveway Spaces
  • Parking Storage or Cabinetry
  • Front Facing Garage

Property Views

  • Woods
  • Garden

Home Design

  • Contemporary Architecture
  • Slab Foundation
  • Frame Construction
  • Shingle Roof
  • Stick Built Home

Interior Spaces

  • 8,057 Sq Ft Home
  • Property has 3.5 Levels
  • Vaulted Ceiling
  • Ceiling Fan
  • Recessed Lighting
  • Entrance Foyer
  • Great Room
  • Dining Room
  • Loft
  • Bonus Room
  • Solarium
  • Storage Room
  • Utility Room

Kitchen

  • Built-In Double Oven
  • Electric Oven or Range
  • Cooktop
  • Microwave
  • Extra Refrigerator or Freezer
  • Dishwasher
  • Kitchen Island

Flooring

  • Engineered Wood
  • Carpet
  • Concrete

Bedrooms and Bathrooms

  • En-Suite Primary Bedroom
  • En-Suite Bathroom
  • Walk-In Closet
  • Walk-in Shower

Laundry

  • Laundry Room
  • Laundry on upper level
  • Dryer
  • Washer

Accessible Home Design

  • Accessible Elevator Installed
  • Grab Bars

Pool

  • Indoor Pool
  • Pool and Spa

Outdoor Features

  • Multiple Balconies
  • Patio
  • Wood or Metal Shed
  • Outbuilding
  • Playground

Additional Homes

  • Guest House

Utilities

  • Forced Air Zoned Heating and Cooling System
  • Ductless Heating Or Cooling System
  • Back Up Gas Heat Pump System
  • Heating System Powered By Owned Propane
  • Wall Furnace
  • Water Treatment System
  • Well
  • Propane Water Heater
  • Capping Fill
  • Low Pressure Pipe

Community Details

  • No Home Owners Association

Listing and Financial Details

  • Assessor Parcel Number 235-25.00-68.00

Home Details

Home Type

Single Family

Est. Annual Taxes

$4,567

Year Built

Built in 2006

Lot Details

0

Parking

6

Listing Details

  • Property Type: Residential
  • Structure Type: Detached
  • Architectural Style: Contemporary
  • Sussex De Quadrants: Between Rt 1 & 113
  • Accessibility Features: Elevator, Grab Bars Mod
  • Ownership: Fee Simple
  • New Construction: No
  • Story List: Lower 1, Main, Upper 1, Upper 2
  • Federal Flood Zone: No
  • Year Built: 2006
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Appliances: Cooktop, Dishwasher, Microwave, Oven - Wall, Oven/Range - Electric, Oven - Double, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer
  • Flooring Type: Engineered Wood, Concrete, Carpet
  • Interior Amenities: Bathroom - Stall Shower, Bathroom - Walk-In Shower, Carpet, Ceiling Fan(s), Dining Area, Elevator, Kitchen - Island, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), Water Treat System
  • Fireplace: No
  • Wall Ceiling Types: 2 Story Ceilings, 9'+ Ceilings
  • Foundation Details: Slab
  • Levels Count: 3.5
  • Room List: Dining Room, Primary Bedroom, Bedroom 3, Bedroom 4, Kitchen, Foyer, Bedroom 1, Great Room, Laundry, Loft, Solarium, Storage Room, Utility Room, Bonus Room, Primary Bathroom, Full Bath
  • Basement: No
  • Laundry Type: Upper Floor
  • Total Sq Ft: 8057
  • Living Area Sq Ft: 8057
  • Price Per Sq Ft: 155.08
  • Above Grade Finished Sq Ft: 8057
  • Above Grade Finished Area Units: Square Feet

Beds/Baths

  • Bedrooms: 4
  • Main Level Bedrooms: 1
  • Total Bathrooms: 5
  • Full Bathrooms: 5
  • Main Level Bathrooms: 1.00
  • Upper Level Bathrooms: 3
  • Lower Levels Bathrooms: 1
  • Upper Level Bathrooms: 2.00
  • Upper Level 2 Bathrooms: 1.00
  • Lower Levels Bathrooms: 1.00
  • Main Level Full Bathrooms: 1
  • Lower Level Full Bathrooms: 1

Exterior Features

  • Other Structures: Above Grade, Below Grade
  • Other Structures List: Guest House, Shed, Wood/Metal Shed
  • Construction Materials: Frame, Stick Built
  • Exterior Features: Extensive Hardscape, Outbuilding(s), Play Area, Secure Storage, Underground Lawn Sprinkler
  • Pool Features: Indoor, Pool/Spa Combo
  • Roof: Shingle
  • View: Garden/Lawn, Trees/Woods
  • Water Access: No
  • Waterfront: No
  • Water Oriented: No
  • Pool: Yes - Personal
  • Tidal Water: No
  • Water View: No

Garage/Parking

  • Garage Spaces: 6.00
  • Garage: Yes
  • Parking Features: Asphalt Driveway
  • Garage Features: Garage - Front Entry, Inside Access, Oversized, Additional Storage Area
  • Attached Garage Spaces: 4
  • Number Of Detached Garage Spaces: 2
  • Total Garage And Parking Spaces: 16
  • Type Of Parking: Attached Garage, Driveway, Detached Garage
  • Number of Spaces in Driveway: 10

Utilities

  • Central Air Conditioning: Yes
  • Cooling Fuel: Electric
  • Cooling Type: Central A/C, Zoned, Ductless/Mini-Split
  • Heating Fuel: Electric, Propane - Owned
  • Heating Type: Heat Pump - Gas Backup, Wall Unit, Zoned
  • Heating: Yes
  • Hot Water: Propane
  • Sewer/Septic System: Capping Fill, Low Pressure Pipe (LPP)
  • Water Source: Well

Condo/Co-op/Association

  • Condo Co-Op Association: No
  • HOA: No
  • Senior Community: No

Schools

  • School District Source: Listing Agent

Lot Info

  • Lot Features: Trees/Wooded, Private
  • Lot Size Acres: 7.47
  • Lot Dimensions: 225.00 x 1074.90 x 399.23 x 1035.44
  • Lot Size Units: Square Feet
  • Lot Sq Ft: 325393.00
  • Outdoor Living Structures: Balconies- Multiple, Patio(s)
  • Zoning: AR-1
  • In City Limits: No

Rental Info

  • Vacation Rental: No

Tax Info

  • School Tax: 4154.00
  • School Tax Pymnt Freq: Annually
  • Tax Annual Amount: 4567.00
  • Assessor Parcel Number: 235-25.00-68.00
  • County Tax Payment Frequency: Annually
  • Tax Year: 2024

MLS Schools

  • School District Name: CAPE HENLOPEN

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $2,229 $92,650 $3,750 $88,900
2024 $4,317 $92,650 $3,750 $88,900
2023 $4,313 $92,650 $3,750 $88,900
2022 $4,154 $92,650 $3,750 $88,900
2021 $3,963 $92,650 $3,750 $88,900
2020 $3,950 $92,650 $3,750 $88,900
2019 $3,956 $92,650 $3,750 $88,900
2018 $3,669 $92,650 $0 $0
2017 $3,496 $92,650 $0 $0
2016 $3,201 $92,650 $0 $0
2015 $3,036 $92,650 $0 $0
2014 $3,010 $92,650 $0 $0
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
09/27/2025 09/27/25 Price Changed $1,249,500 -3.8% $155 / Sq Ft
09/09/2025 09/09/25 Price Changed $1,299,500 -3.7% $161 / Sq Ft
08/26/2025 08/26/25 Price Changed $1,349,500 -3.3% $167 / Sq Ft
08/08/2025 08/08/25 For Sale $1,395,000 -- $173 / Sq Ft
Source: Bright MLS

Purchase History

Date Type Sale Price Title Company
Deed -- Fuqua Williard & Schab Pa
Deed $80,000 --
Source: Public Records

Source: Bright MLS

MLS Number: DESU2091770

Bright MLS

APN: 235-25.00-68.00